(Z)-7-((1S,2R,3S,4R)-3-Methylsulfanylmethylsulfanylmethyl-7-oxa-bicyclo[2.2.1]hept-2-yl)-hept-5-enoic acid methylsulfanylmethyl ester | 119694-89-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (Z)-7-((1S,2R,3S,4R)-3-Methylsulfanylmethylsulfanylmethyl-7-oxa-bicyclo[2.2.1]hept-2-yl)-hept-5-enoic acid methylsulfanylmethyl ester
• CAS: 119694-89-2
• 化学式: C₁₈H₃₀O₃S₃
• 分子量: 390.632
• InChiKey: YMUAFTMKWUSQTL-WFOZZGTHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.81
• 重原子数：
  24.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (Z)-7-((1S,2R,3S,4R)-3-Methylsulfanylmethylsulfanylmethyl-7-oxa-bicyclo[2.2.1]hept-2-yl)-hept-5-enoic acid methylsulfanylmethyl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 8.5h， 以46%的产率得到<1S-<1α,2α(Z),3α,4α>>-7-<3-<<<(Methylthio)methyl>thio>methyl>-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoic acid
  参考文献：
  名称：

  9,11-Epoxy-9-homo-14-thiaprost-5-enoic acid derivatives: potent thromboxane A2 antagonists

  摘要：

  A novel bicyclic prostaglandin analogue, (1S)-[1 alpha,2 alpha(Z),3 alpha,4 alpha]-7-[3-[(hexylthio)methyl]-7- oxabicyclo [2.2.1]hept-2-yl]-5-heptenoic acid ((-)-10), and its cogeners were found to be potent antagonists at the TxA2 receptor. Compound (-)-10 was the only stereoisomer out of eight possible structures that was active. Thioether (-)-10 was 30-40-fold more potent than another TxA2 antagonist, BM 13.177, in inhibiting arachidonic acid (AA) induced aggregation of human platelet-rich plasma. Compound (-)-10 was effective (I50 = 0.5 +/- 0.4 microM) in inhibiting 9,11-azo-PGH2-induced (0.1 microgram/mL) contraction of guinea pig tracheal spirals. The bronchoconstriction in anesthetized guinea pigs induced by AA was also effectively antagonized by (-)-10 (1 mg/kg, iv); however, in this assay (-)-10 exhibited some direct agonist activity. Radioligand binding studies in washed (human) platelets revealed that (-)-10 is one of the most potent ligands for the PGH2/TxA2 receptor yet described (Kd = 1.6 +/- 0.4 nM).

  DOI：

  10.1021/jm00125a009
• 作为产物：
  描述：

  [1S-[1α,2α(5Z),3α,4α]]-7-[3-(hydroxymethyl)-7-oxabicyclo[2.2.1]hept-2-yl]-5-heptenoic acid, methyl ester 在 吡啶 、 氢氧化钾 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 、 xylene 为溶剂， 反应 1.92h， 生成 (Z)-7-((1S,2R,3S,4R)-3-Methylsulfanylmethylsulfanylmethyl-7-oxa-bicyclo[2.2.1]hept-2-yl)-hept-5-enoic acid methylsulfanylmethyl ester
  参考文献：
  名称：

  9,11-Epoxy-9-homo-14-thiaprost-5-enoic acid derivatives: potent thromboxane A2 antagonists

  摘要：

  A novel bicyclic prostaglandin analogue, (1S)-[1 alpha,2 alpha(Z),3 alpha,4 alpha]-7-[3-[(hexylthio)methyl]-7- oxabicyclo [2.2.1]hept-2-yl]-5-heptenoic acid ((-)-10), and its cogeners were found to be potent antagonists at the TxA2 receptor. Compound (-)-10 was the only stereoisomer out of eight possible structures that was active. Thioether (-)-10 was 30-40-fold more potent than another TxA2 antagonist, BM 13.177, in inhibiting arachidonic acid (AA) induced aggregation of human platelet-rich plasma. Compound (-)-10 was effective (I50 = 0.5 +/- 0.4 microM) in inhibiting 9,11-azo-PGH2-induced (0.1 microgram/mL) contraction of guinea pig tracheal spirals. The bronchoconstriction in anesthetized guinea pigs induced by AA was also effectively antagonized by (-)-10 (1 mg/kg, iv); however, in this assay (-)-10 exhibited some direct agonist activity. Radioligand binding studies in washed (human) platelets revealed that (-)-10 is one of the most potent ligands for the PGH2/TxA2 receptor yet described (Kd = 1.6 +/- 0.4 nM).

  DOI：

  10.1021/jm00125a009